


the sapphire will see you now

by AbeTheDadtm



Category: Critical Role (Web Series)
Genre: Anal Play, Blow Jobs, Bondage, Creampie, Cunnilingus, Dirty Talk, Discussion of sexual assault, Dom/sub, F/F, F/M, First Time, Gentle Sex, Impact Play, Kinktober 2018, Knotting, Light Bondage, Light Dom/sub, Name-Calling, Nonbinary Character, Other, Rope Bondage, Rough Sex, Sex Toys, Sex Work, Trans Character, Trans Female Character, Trans Male Character, Vaginal Fingering, Vaginal Sex, Voyeurism
Language: English
Status: In-Progress
Published: 2018-10-24
Updated: 2018-11-14
Packaged: 2019-08-07 02:08:39
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 18,034
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16399379
Author URL: https://archiveofourown.org/users/AbeTheDadtm/pseuds/AbeTheDadtm
Summary: Originally a prompt for Kinktober (number eight: sex work).The Sapphire is a courtesan, much like her mother, well known for her playful nature. When several wedding parties arrive at the Lavish Chateau, she gets to be a part of the new relationships, the old regrets, and the self-discovery.





	1. violet and cornflower

**Author's Note:**

> Yes, I'm super behind. Yes, this is gonna be a new project. Enjoy.

The Sapphire of the Sea was in high demand this season. She was in high demand most seasons, of course. The Ruby’s daughter was much like her mother, except the Ruby’s mature elegance and grace was replaced with youthful energy and a bubbly spirit. She had people of all sorts lining up, spending hundreds of gold coins just to see her dance, to hear her sing, to take her to bed. But no one ever caught her eye. Jester was visited by people of many races, ages, genders, body types, cultures. She had slept with all sorts of tieflings, several people from Xhorhas, all sorts of nobles. When she saw her next client was a noble of the House Tealeaf, she didn’t pay it any mind, simply got dressed in the pretty scarlet negligee that brought out the blue of her skin and draped herself in silks and laid on the bed, perfectly posed.

But then they walked in.

They were tall, bearded, with long, well-tended curls that poured in a braid down their back. Their eyes were the same deep scarlet as the lace that clung to her body, and their clothes...they wore dozens of colors, a long red coat embroidered with every symbol of every religion and house and nation she’d ever heard of, and some she hadn’t, a waistcoat made of a patchwork of fabrics, tight around his round stomach, striped pants that clung to round thighs. Jester let her seductive gaze dropped in favor of one of complete surprise. “Are you Mx. Tealeaf?” she asked.

“Yes, that is me,” said Mx. Tealeaf. He stepped forward and extended his hand, which Jester took gently. “Mollymauk Tealeaf. But please, call me Molly.”

“Molly. That’s a pretty name.” She sat up on her knees, hands placed just so on her thighs.

“Thanks,” said Molly as he sat down on a plush chair. “I chose it myself.”

“Oh?” Jester’s eyebrow raised, and her serene expression slipped into a happy, curious one.

“It’s a bit of a long story, but the short of it is I was found by the former head of the Tealeaf house, Gustav, and when I needed a name, I chose Mollymauk. It sounded right at the time, and it still works today, apparently.” They laughed, and it was hearty, filling the quiet of the room like wine filled a glass. 

“Well, I chose mine, too,” said Jester. “But! That’s a story for another time. This is about you and what you want.” She tried to keep her tone serious, stern, more like her mother’s, but Jester couldn’t help wiggling a bit as she spoke, anxious to start. “First of all, do you have any limits? Is there anything I should not do?”

Molly nodded, leaning forward, rubbing their thighs. “Blindfolds, gags, bondage. I don't mind you getting tied up, but I don't like it myself. Tight spaces, breathplay. Anything involving playing dead. Use of any name besides my own.”

Jester nodded, trying not to judge but instinctively trying to piece together what all this originated from. Whatever it was, she couldn't piece it together. She stood and moved towards the center of the room, towards some fine silk cushions next to a marble table. “Please, undress and sit, then we can start the blessing ceremony.” She sat down, on her knees once again, tapping her thumbs against her thighs. Jester very much wondered what Molly looked like under their colorful clothing.

They stood and took off their coat, then their waistcoat, then a baggy white shirt with swirling embroidery around the hem and the cuffs. Their chest underneath had dark violet hair, dark enough that it looked black, but its true color could be revealed in the right light. They took off boots with embossed flowers and dyed laces, pulled over soft, knitted socks. Jester bit her lip in anticipation as Molly unbuckled their belt and unlaced their trousers. They hooked thumbs under their trousers and small clothes, wiggling a bit to get them past their ass and thighs. When they stood to kick off their pants, they revealed a pretty tiefling cock with ridges and a spade tip, crowned with dark hair and pierced along the shaft and tip. Had she not been raised right, Jester would've taken that cock in her mouth right away, but instead, she just pointed to the cushion before her as she took a sketchbook and pencil from the table next to her.

They sat before her, originally cross-legged. “Should I pose?” they asked.

“Whatever you're comfortable with,” Jester replied.

Molly nodded and shifted to lean against the wall, one knee up and one leg stretched out. Jester began to sketch as she silently prayed to the Traveller, dedicating her energy, the drawing, and the sacred activity that would occur shortly to him, feeling his presence fill her up with a bubbly energy.

“If I may ask,” said Molly, voice deep and serene, “what is this for exactly?”

“It's an opportunity to worship my god, the Traveller.” Had she not been better trained, she would've rattled his ear off about her god. But she knew better than that now. “House Tealeaf worships the Moonweaver, right?”

“Yes, we do,” said Molly.

“Good thing this was scheduled for the full moon. We can open the curtains and fuck in the moonlight.”

“That sounds lovely,” Molly said with a smile Jester just had to capture. 

She worked diligently, struggling a bit to capture the crooked point of their nose, adding tiny patches of hair with delicate strokes of the pencil, giggling a bit as she sketched their cock. When she was done, she showed it to him. “Do you like it, Molly?” she asked.

They smiled wide when they saw it. “That is the prettiest thing I've ever seen, Miss Jester.”

Jester laughed as she closed the sketchbook. “Really?” she asked.

“Absolutely,” they said.

“Well, then get on the bed Mx. Molly. I'll get things ready for you.”

Molly obeyed, slipping onto the bed. Jester lit the candles and dimmed the gas lights, making the room a dim orange. She opened the curtains, revealing the moonlight, and it made her blue form appear even more vibrant. Her tail swayed like a cat’s, and she detected a mirrored motion in his tail. She smiled and approached the foot of the bed, close enough that he could touch her if he reached out from where he sat, but far away enough that he’d have to make an effort to do so. Illuminated by moonlight and silhouetted by candlelight, Jester started to undress, slowly slipping off the negligee down the fat of her tummy, shimmying it past her ass and thighs before it pooled at her feet, revealing bare skin with stretch marks trailing along her tummy and thighs and breasts. Molly smiled. “I’m lucky I was able to meet with such a vision as yourself.”

Jester giggled. “Thank you.” She almost brushed off the compliment, said something like “I’m not nearly as pretty as my mom,” but she bit her tongue, knowing how annoyed she got when handsome men or pretty women avoided her compliments.

Slowly she crawled onto the bed next to them, and they leaned back, watching her with those pretty red eyes of theirs. “May I touch?” they asked.

“You may,” she said, inching closer until she could feel their breath.

They smiled, leaned in, and kissed her, soft at first, hand going to her neck as she leaned ever so slightly on their chest. They shifted so that Molly was on their back and Jester was straddling their stomach, and they kissed hungrily, sharing warm breaths and firm touches. Their hands went to her thighs, rubbing at the plush fat and strong muscle. After a while, Jester slipped off their stomach, slid down, and positioned herself in between their legs.

Molly moved a couple of pillows underneath them so they could lean up and see her. She gently wrapped a graceful hand around their cock. Her claws were filed down, so they only felt soft skin on their ridges, slowly moving up. She smiled, and it looked so pretty in the moonlight. Molly groaned, grinning.

“Does it feel good?” she asked, smiling wide, lips close enough to their cock that they just graced one of the ridges as she spoke.

“Feels damn good,” Molly said. Her mouth slipped down, down, down their cock until she had him up to the hilt. Molly’s head fell back and they moaned as she bobbed back up again. “Holy fucking shit,” they muttered. “Gods, that’s gorgeous.”

“Thank you,” Jester said, drool slipping down her lips and chin, smudging her dark pink lipstick. “You look very pretty, by the way.”

“Yes, thank you, keep going please,” said Molly, voice strained and desperate.

Jester nodded and went back to sucking their dick. She bobbed, licked, sucked, explored around their ridges and piercings. Every movement of her tongue was expertly trained, bringing on euphoric bursts of sensation to Mollymauk’s cock. Their breath got huffy and their voice got tight. “Jester, Jester, I’m close…”

“Come on my face, pretty one,” said Jester, tail lashing in excitement.

Warmth and pleasure coiled in between Molly’s legs, then exploded in a burst like a berry squeezed between fingers. Come spurted onto Jester’s face. She stretched out her tongue and caught some of it, smiling with the warm, heady taste of it. 

Once he was done, she wiped off her face with a towel from the nightstand. Some of her makeup wiped off too, but she didn’t mind so much. In the dimness of the room, Molly would barely notice anyway. “What would you like to do next?” she asked.

Molly thought for a moment, breath panting, mind still whirring from the high of orgasm. “Maybe I can eat you out?”

“You don’t have to,” Jester said.

“Maybe I want to.” Their eyebrows raised up and they grinned. 

Jester smiled and slipped up onto the bed next to them. Molly reached around and held Jester in their arms as they kissed. “You’re so gorgeous,” they said, grabbing and kneading at Jester’s breasts.

“Thank you,” she replied, kissing at their jaw and neck. They moaned softly. “Mind if I leave a mark? I’ll be careful with my fangs.”

“Feel free,” said Molly, baring their neck for her.

Jester eagerly sucked at their skin until a dark violet mark formed on their neck. She wiped it off, admired it. “It’s going to look very pretty when it darkens.”

“I’m sure it will.” Molly kissed her neck this time, letting their kisses trail downwards to her breasts. They paused to bite and nip and suck at them, leaving a dark blue mark on the inside of her breast.

“Now we're both going to look pretty,” Jester said.

“Yes, we are indeed.” Molly continued moving downwards, kissing her tummy, taking a bit of time to kiss the stretch marks around her belly button. They kissed at her hips, hopped between thighs, then finally, finally, lapped at her cunt. 

Jester exhaled deeply and held Molly’s horn in her hand, squirming a little in the hope of getting more.

“So impatient,” Molly teased, then began lapping at her labia, the entryway to her cunt, everywhere that wasn’t her clit.

She held onto their horns, trying to direct them up, but Molly was just as stubborn as she was. “Just suck my clit, you ass,” she said, a bit sharply.

Molly’s head popped up. “Now, maybe, if you put your hands above your head and stayed quiet, maybe I’ll suck your clit.”

Jester grumbled but obeyed, laying back and raising her hands above her head, chewing on her lower lip.

“There we go,” said Molly cheerily before licking one long stripe over her clit. Then another. Then another. Then they sucked on her clit and Jester saw stars.

A sharp moan escaped from her, and her back arched and eyes scrunched closed. “Fuck, Molly!” she squealed.

Molly kept going, intent on making her come. It wasn't long until they succeeded. Her thighs clamped around their face, squishing their soft cheeks as she screamed with pleasure.

When she was done, they came up for breath. “Holy shit, Jester,” they said, laughing.

“You’re amazing,” said Jester, panting and giggling.

Molly smiled and slipped up to her, kissing her. She could taste her wetness on their lips, a thick, heady flavor that she personally enjoyed. They kissed for a long while, arms entwined around each other, just being together in a way that Jester enjoyed. “I like this,” she said. “You better come back, because you are a lot more fun than most of the people who come in here.”

“Ah, well, I probably won’t be able to for very long,” said Molly, a little sad.

“Why not?” Jester frowned.

“Because I am to be married next month.”

“Oh? Is that why you’re here?” Jester heard whispers of a wedding happening in the big temple for all of the gods, the one that wasn’t far from her home. But she hadn’t known who was getting married.

“Mmhm. To the young Caleb Widogast of House Widogast. Our houses have been feuding for a long time, we’re around the same age, together we can have children, so it was determined to be a good match. But I’ve only just met him and I’ve already fucked things up.”

“How? You’re super nice and charming.”

“Not when it matters, it seems,” said Molly, sighing. “I asked him about his parents. Apparently, they died. Some mysterious illness tore through them when Caleb was young. He got it too but didn’t die. Always blamed himself for it, according to his friend Nott. But I asked when they were coming to the wedding and he rushed off crying.”

“Ah,” said Jester. “I see your problem.”

Molly chuckled sadly. “Yeah. Foot, meet mouth.” They sighed and laid down on their back, looking up at the ceiling. “It’s a shame, too, because he’s damn attractive. I mean, he’s shy as you can get, but he’s incredibly handsome. Got a good beard, nice face. The prettiest blue eyes you’ll ever see.”

“Prettier than mine?” Jester asked.

“I mean this in the nicest way possible, but yes.”

Jester giggled. “You have it bad for him.”

Molly nodded. “Yeah. Yeah, I do. Too bad I messed it up.”

“You can always fix it,” Jester said. “Just apologize and move on.”

“I know, I know.” He sighed. “It’s just hard. A lot of stuff depends on this marriage working out. It wasn’t long ago that our countries were going to war. If we went to war again...I don’t know what we’d do.”

“You’ll figure it out. You’re smart. And I can help too.”

“You would?”

Jester nodded. “Of course, Molly. We got a lot more pull here than you’d think, Mx. Tealeaf.” She winked and giggled. “Are you two staying here?”

“Yes. There’s no other place in the Menagerie Coast worth our gold.”

“You flatter us, Molly,” Jester giggled. 

“Well, that’s part of my job,” said Molly. He smiled and kissed her again.

“You want to continue?” Jester asked.

Molly nodded. “Yes, please.”

Jester looked down and saw that he was hard again already. “Damn. You’re fast.”

“Honestly? I might’ve been imagining me with a certain red-haired noble.”

With a giggle, Jester said, “Silly, you’re supposed to be fantasizing about me.”

“Well, I’m a rebel.” Molly stuck out their chin.

“You little brat,” said Jester as she leaned down for a kiss. She shifted to straddle them, slowly slipping their cock into herself. Her back arched and she moaned. It had been a while since she’d had a good tiefling cock inside of her, and she’d forgotten how good it was.

“You feel about as good as you taste,” said Molly once they were fully inside her.

“I hope that’s a good thing,” Jester said, smiling.

“You’ll have to figure that one out for yourself,” said Molly with a wink.

Jester smiled and slowly began to move up and down on Molly’s cock. “Can you sit up a little? I want my clit to hit your stomach but it’s kind of hard at this angle.”

Molly grabbed another pillow and added it to the pile behind them, bettering the angle of their stomach.

“That’s better,” she said. Her clit now bumped more against their tummy as she ground up against them, and it sent sparks of pleasure down her cunt. She could feel the ridges inside of her, pressing against her walls. “Fuck, Molly,” said Jester and she picked up the pace.

Their hands rubbed her thighs, fingers pressing against her stretch marks and downy patches of body hair. Her hands explored the thick hair on their chest, her fingers toyed with the golden nipple piercings shaped like little moons. Then they came together and kissed. It was nice, warm skin against warm skin, soft against soft.

Slowly, Jester’s breath became more hitched. A hand reached down, and purple fingers pressed against her clit. She yelped sharply as they rubbed at her, then quickened her pace, desperate for more. The sparks became flame, burning between her legs, then she came with a scream, gushing a little.

“What a show,” they said with a laugh.

“Thank you,” said Jester, smiling. “Where would you like to come?”

Molly thought for a moment. “Maybe on that pretty face of yours?”

She nodded and slipped down to the floor. They moved to the edge of the bed, pumping their cock with one of their big hands. With a deep groan and a roll of the head, they came, splattering warm white seed over her face. Jester smiled and went to grab a towel. “That was fun.” She wiped her face and hair clean.

“That was,” Molly said, falling onto their back. 

“Why don’t I get a robe for you? We can drink some tea downstairs.”

“Sounds lovely.”

Jester got a robe from the little closet she had for guests. It was baggy and a bit long, but the color was a brilliant emerald green, and it showed off their lovely chest hair. The two went downstairs into the lobby, where there were various tables and chairs, some open to the windows and the rest of the room, some hidden by colorful fabrics hanging from the ceiling. The room was mostly empty, save for a few milling servants in pretty outfits and a handful of guards assigned to the nobles staying there. Jester took Molly’s hand and giggled. “Here. Let me show you my favorite spot.”

“Shit,” Molly said, freezing. There was a red-haired nobleman sitting in one of the more cocooned tables, book before him. He looked up at him. Molly hadn’t been kidding when he said he was handsome. Soft face, fuzzy, well-trimmed beard, wavy shoulder-length hair, pretty blue eyes. His face dropped and he gathered his book, leaving quickly and curtly. Molly groaned as they sat down. “Damn it.”

“I’m sorry, Molly.”

“It’s not your fault, Jester. I’m going to go to bed now.” They sighed, rubbing the back of their neck. “Have my clothes sent to my room, please. Thank you for tonight.”

“Of course,” said Jester, watching them as they disappeared up the stairs.


	2. different shades of blue

“How many weddings are happening, Mama?” Jester asked as Sprinkle raced up her shoulders and settled behind her hair. “It feels like there’s so many.”

“Four,” said the Ruby.

Jester nodded and continued brushing Marian’s hair. “That’s a lot.”

“Yes. And they’re all staying here.” Marian preened a little.

“All of them?” Jester’s mouth dropped.

“We’re the closest inn to the Grand Temple,” said Marian, “and we’re the finest inn in Nicodranas if I do say so myself.”

“Of course we are, Mama,” Jester said with a smile.

“Anyways, I bring this up because a lot of our clients are going to be involved in the weddings. You’ll have to be at your very best to impress, but you don’t want to make waves and cause trouble, as much as you want to. Okay, Jester?”

Jester sighed. Trouble was her specialty. But trouble could wait. “Okay, Mama. I’ll try.”

“Thank you, Jester.” Marian reached back and patted her on the knee. “Your client tonight is one of the brides. Beauregard of House Lionett. She’s the heir to the House. Getting married to a member of House Widogast, Astrid Linnemann. Rumor has it they’re not...the happiest about the situation, so try not to cause any stress on their relationship, okay?”

“I’ll try, Mama.”  
\----------  
That night, Jester chose to wear a baby pink ensemble, a pretty lace bra and short, soft knickers that hugged her ass really well. She grabbed a rose-colored robe and wrapped it around herself, sitting down again on the bed. The wind came in through the windows and made the curtains around her bed shift softly.

Beauregard came in through the door and Jester was surprised. The woman who came in was tall and muscular, with broad shoulders and strong pecs. Her hair was long and tied up, revealing fuzzy shaved hair on the underside of her head. She wore turquoise robes and harem pants that fell around her body, showing off quite a bit of skin for a woman about to be married. Jester smiled. “Are you Miss Beauregard Lionett?” Jester asked.

“Yeah, that’s me,” said Beau in a husky voice.

“Sit down, please,” said Jester, pointing to the chair by the bed.

Beau obeyed, sitting with one leg over the arm of the chair and one leg sticking out. 

“Now. This is when we usually talk about hard limits. Things you don’t want me to do. I don’t have any. Do you?”

“Just don’t call me names and I think we’ll be good,” said Beau. 

Jester nodded. “Okay. Now undress, sit down over there, and we’ll start the blessing ceremony.”

“Alright.” Beau got up and undressed. She was covered, head to toe, in rippling muscles. They weren’t thick, hefty ones, but they were glorious. The woman’s cock hung low. The hair around it was shaved, and it was uncut. It was pretty. She sat down, one leg up and slightly bent, the other folded under it. Beau leaned on the knee, watching as Jester took her sketchbook. “You draw?” she asked.

“And paint,” said Jester. “I paint all of the sketches I make in between appointments. It’s nice. It helps me remember things. I’ve always joked that one day I’ll open a gallery with all of them, but it’d be too big because I have too many.” She giggled. Beau laughed a little. It was a nice, deep chuckle. “But Mama would never let me. Too many important people would get mad.” Jester started sketching. 

“Yeah, that’s fair,” said Beau. She sighed, face going dark. “I know how it feels, wanting to do something but not being able to because other people would get mad.”

“Oh?”

Hesitantly, Beau continued, “I’m in love with someone other than the woman I’m supposed to marry. She’s the guard of the Tealeafs, Yasha. But I could never marry her.”

“Why not?” Jester asked.

“My parents would disown me,” said Beau, sadly.

“So?”

“I can’t do anything without them. I’d have no money, no job...no anything.”

“Oh.” Jester frowned. “I’m sorry. If you ever wanted to do it, though, we’d be happy to help.”

“Thank you. It’s nice to hear that.” Beau rubbed her knee.

“So…” said Jester with a big smile. “Tell me about her.”

Beau practically talked her ears off. Her name was Yasha. She was really tall, with really pretty dark hair that faded into white, and muscular, and sweet, and she collected flowers. The two had been together before, many a time, whenever House Tealeaf came over to her family’s estate to do business. She was Molly’s favorite, apparently. 

“She sounds interesting,” said Jester. “You like her?”

“Yeah. A lot.”

“How long have you two known each other?”

For a moment, Beau paused, looking up as though she were counting. “Two years?”

“Two years isn’t bad,” said Jester. “My mother knew my father for a lot less and she still knew it was love. Sometimes you just know, you know?”

“Yeah, that’s what it’s like,” said Beau. “Have you ever been in love?”

“Not yet, I haven’t.”

“Ah,” said Beau. “Yeah, uh. Good look if and when it happens to you. It’s...not the easiest to deal with.”

“I know that already.” She had seen how her mother still loved her father, even after all these years of him being away. 

The two fell into silence. Jester sketched. Beau watched. It was nice. She turned to show it to Beau. “You like it?” she asked.

Beau nodded. “It looks really good.” She sighed a little. “I wish my body looked a little more...you know.”

“Feminine?”

“Uh huh.”

Jester sighed, unable to help. “I like the way you look. You have really nice skin.”

“Thank you.”

With a smile, Jester said, “It’s no problem.” She closed her book and set it aside. “So. Why don’t you get on the bed while I get undressed?”

“Your wish is my command,” Beau said with a smile. She strode to the bed and jumped onto it, smiling wide as she did so.

Slowly, Jester approached until she stood at the foot of her bed. The robe fell from her shoulders. She removed the bra, then the knickers. 

Beau sat up. “Wow.”

“Thank you!” Jester climbed on the bed, and Beau pulled her in for a kiss. It was nice. Beau’s lips were surprisingly soft and very warm. The two embraced, and Jester pushed Beau onto her back. “Want me to suck your...what do you call it?”

“I just call it a cock,” said Beau, shrugging. “Might as well call a spade a spade. Rather do that than invent some fancy word for it when everyone knows what you mean.”

“Fair,” said Jester. “Do you want me to suck your cock?”

“Not really to be honest,” said Beau. “I’m not super comfortable having attention being called to it. You can sit on my face though.”

“Alright,” said Jester. She grinned, unused to getting such fine treatment. Screw what people said about the younger generation; they were a lot more willing to eat her out than the old men who made appointments with her. “Want me to be facing the headboard or the foot of the bed?”

“Headboard,” Beau decided.

Jester straddled Beau’s head, facing the headboard and the wall. Warm hands held her hips and Beau’s blue eyes looked up at her as her tongue lapped at Jester’s pussy. “Fuck,” Jester moaned, head rolling back, eyes closing. “You’re really good at this.”

“I’ve gotten a lot of practice,” said Beau with a grin. She was right. The woman sucked Jester’s clit in a way that made her twitch. Jester ground into Beau’s mouth.

“Can I grab your hair?”

Beau made a sound of approval and Jester pulled Beau’s hair as she moaned, eliciting a happy noise from Beau.

Quickly, Beau wrenched an orgasm out of Jester, then another, leaving her a moaning, twitching, sensitive mess. “Lucky Yasha,” Jester said with a grin.

“Indeed,” Beau said.

Jester moved to the side and let Beau sit up. She handed Beau the towel by her bed to wipe her face off. “So? What next?”

“We can have like...actual sex, I guess.” Beau shrugged.

“That sounds like a good idea,” said Jester, smiling. “What sort of position are you thinking?”

“From behind? That would be nice.”

As she got into position, Jester giggled excitedly.

Beau got up behind her and took a moment to suck and lap at her cunt. 

Jester squealed. “You’re supposed to fuck me, silly!” she said.

“Are you complaining?” Beau asked.

“Not really,” Jester said in between moans. 

When Beau was satisfied, leaving Jester on the edge, she took her time cleaning her up, barely touching her.

“Touch me,” Jester whimpered. “Please.”

“Maybe,” said Beau. She took her cock in her hand and started rubbing it. “Let me get hard first,” she said. Jester watched as she rubbed her cock. Beau made short little moans and sharp breaths as she jacked off. It was driving Jester insane with want.

“Please fuck me,” Jester whined. “You’re hard now. You can do it.”

“I’m the one paying,” said Beau, “I’m the one who decides.” She took a strong finger and slipped it into Jester’s cunt, not moving it. Jester tried to fuck herself on it but it wasn’t enough, wasn’t good enough.

“More, please?” she begged.

“Beg more.”

“Please, Beau, please,” said Jester as she ground up against Beau’s hand, gripping the sheets, head half-buried in the pillows. “Please, fuck me with your fingers, your cock, anything.”

Beau smiled and slapped her ass, a bit tentatively. Jester moaned, gasping sharply. With a grin, Beau said, “Good girl. If I slap you four more times you get another finger. Okay?”

Jester nodded. “Yes, ma’am.”

One slap hit, still tentative, testing things out. “Good?” Beau asked. “You want more?”

“Please.”

Another. This one stung slightly. “More?”

“Yes, by the Traveller, yes,” said Jester. 

The next slap hurt more, but the feeling was good. It sent electric shocks straight to her cunt. “More?”

“Go as hard as you want, Beau,” said Jester.

“Alright.” Beau hit her, really hard, and Jester squealed and bit the pillows. “That good?”

“Really good,” Jester giggled.

“Good. Since you were so good through that, I’ll give you two more fingers. Okay?”

Jester nodded. “Yes, please!”

Beau entered three fingers into her, pumping them hard. Jester cried out with pleasure. With the sound, she went harder, rubbing at that sweet spot.

“I’m so close, I’m really close, please, please, please let me come!”

“Since you begged so prettily…” Beau slipped another hand under her and rubbed her clit.

With that, Jester came so hard she saw stars. She cried out, toes curling, muscles tensing, then slumped down, undone, panting.

“We’re not even done yet,” Beau said, positioning herself behind Jester’s wrecked form. She wiped off her hands and maneuvered her cock into Jester, and the blue woman cried out.

“Fuck!” Jester yelped. She was so sensitive post-orgasm that the feeling of Beau’s cock made her thighs tense and quake.

With an odd ferocity, Beau fucked into her. One hand pressed into her thigh, grabbing hard enough to surely bruise, and the other hand grabbed her hair, pulling at it roughly as she railed Jester. “You like that? Like the way I fuck into you like that?”

Jester nodded. “Yeah. I do. I like it very -- fuck!” Beau slammed into her just the right way, making her yelp and shake. “Fuck, yes, fuck me right there!”

Beau obliged, slamming her cock into her with a fast rhythm, making an obscene noise that filled the room. “You like that, huh? You little slut?”

“Yes,” Jester cried. “Yes, call me that again.”

“What, a slut? A whore? That’s what you are, you know. That’s what everyone calls you.”

“Gods,” Jester whimpered. An orgasm snuck up on her, and she could only yelp and sob into her pillows, biting down as Beau railed her.

“You came again?” Beau asked. “Gods, you really are a little whore. That’s what, three times now?” A hand came down and slapped her ass once, twice, thrice. It sent shockwaves down to Jester’s cunt. “You like that, huh? Like me playing rough with you like that?”

“Uh huh,” said Jester. Soft and tender sex was all good, but sometimes a girl needed to get railed. “Yeah. I like it.”

“Good. It’s perfect for the little slut you -- fuck, I’m gonna come, I’m gonna come.” She pulled out and pushed Jester down to the bed, and she came onto her back, a pretty white against her blue.

“Fuck,” Jester said. She was gonna be bruised and sore in the morning, but she was proud of herself. “That was incredible, Beau.”

“That was. Thank you. And sorry about all those names. I didn’t mean ‘em.” Beau grabbed the towel from the side and wiped off Jester’s back.

“No, it was fun.” And they’re all true anyway, she thought but didn’t say.

“Oh. Alright. Glad you liked them.”

“Let me get a robe out for you and we can go downstairs and have tea, alright?”

Beau nodded. “Yeah. That sounds nice.”

Jester grabbed her a robe of sapphire blue silk and handed it to her, then dress in her previously discarded pink one. She led her downstairs to one of the tables, and a servant fetched them tea and tiny cakes. “Here, eat one of these. They’re really tasty. This one is strawberry cake, and this one is chocolate, and this one is carrot cake, and this one is vanilla.” She handed the plate to Beau.

“Uh…” Beau grabbed the carrot cake one and ate it in one gulp.

With a giggle, Jester said, “You don’t have to eat it all at once, silly.” She grabbed the chocolate one and ate it, enjoying the sweetness. “Try the vanilla one. It’s really good.” 

“Alright,” said Beau, taking the vanilla cake and eating it, slowly this time. “It is really good. Who makes these?”

“The chef, Alexandria. She’s really good.” Jester ate the last of the cake, then turned to her tea. “Try the tea, too. It’s really good. We get it from House Clay.”

“Don’t they make dead people tea?” Beau’s brow furrowed.

“It’s better than you think, trust me. All of our customers love it.” She leaned in a little. “Though they don’t know it’s dead people tea,” said Jester in a low whisper. “Sometimes I tell them after they drink it if they weren’t any fun.”

Beau chuckled and took a drink of tea. She nodded. “It’s really good.”

Jester added milk and honey to hers and drank some. “Yeah. They’re all really good.” They sat there for a moment, drinking and talking idly, when Jester noticed Beau kept glancing to the side and blushing. “What do you keep looking at?” she asked.

“Oh. It’s just...Yasha’s on duty tonight.”

“Ah!” Jester stood and sought her out. The woman was very tall, quite muscular, and had a mess of hair that faded from black to white. She sat back down and asked, “Do you want to go and see her?”

“She’s on guard! I don’t want to distract her.”

“There are probably guards upstairs watching their room. They’ll be fine!”

With a sigh, Beau said, “Alright, I’ll say hello.” Beau gathered herself and went up to Yasha. Yasha smiled and brought her in for a kiss.

Jester leaned on her arms as she watched the two kiss and hold each other, a little jealous of the two an the feelings they had for each other. Ah, well. She was happy to see people in love.


	3. ginger boy, sapphire girl

They had a party the next night, celebrating the four weddings that would be happening that month. Marian raised a glass and toasted the happy couples, though most of them looked less than happy. Caleb Widogast and Mollymauk Tealeaf looked terribly awkward together, the latter a giant of a person and the former a tiny slip of a thing who would easily be squashed if he wasn’t careful. Beauregard and Astrid were poorly faking smiles. Beau and Jester shared sympathetic glances and had a brief talk behind the stage about everything, but other than that, they didn’t spend much time together. The other two couples were harder to get a read of Aeodwulf of House Tealeaf and Orion of House Clay seemed to get on well, but Aeodwulf kept sharing glances with Astrid that Jester found odd. Meanwhile, Caduceus of House Clay and Calianna of House Draconae seemed to get along like two old friends, sharing wine and friendly conversation and occasional flirtation. Interesting indeed.

While Jester was alone for a while, grabbing cakes from the table of food and stacking them onto her plate, Caleb joined her. “What do you recommend?” he asked. “I am a bit clueless when it comes to food around here.”

“The cakes are really good,” said Jester. “My favorites are the chocolate and strawberry ones, but the vanilla and carrot cake ones are good too.”

Caleb took a carrot cake and ate it almost daintily. “It is really good,” he said between bites.

“You have an appointment with me, don’t you?” Jester asked. “Mama said you did during breakfast. I thought I was free tonight.”

“Oh, if it’s a bother, I can cancel.”

“No, no, it’s no problem. I like my appointments. Well, most of the time, but you seem to be very nice, so I’ll probably enjoy our time together.”

“Ah, okay,” said Caleb. “You see, it’s just that...I’d like some experience before I marry Mx. Mollymauk.”

“I get it,” said Jester, nodding.

“They’re just...so...experienced and casual and...gods, I can’t compare to them. In any way. I’ve never even touched anyone before, much less...have done what you two did.”

“Aw…” Jester said. “I’m honored. But are you sure you want your first time to be with me instead of them? I can invite them along if you want. They can join in or watch or--”

“Nein,” said Caleb, accent sharp. “Sorry. No, thank you. I don’t want them to know I’ve never done this before.”

“Okay,” said Jester. She got all excited. First times were fun, though a bit difficult. She had to be especially good for him and his first time. “Well, I’ll be sure to make sure your first time is really nice, okay?”

“Ja, okay. Thank you, Miss Lavorre.” Caleb took another of the carrot cakes, a bit secretly, and hurried off to join his friends. Aeodwulf and Astrid were sitting at a table with a scary looking man who had been introduced to her as Caleb’s advisor, Mister Ikithon. He was unpleasant looking, with a stern face and a crooked nose, and he looked wickedly at Caleb, like he wanted to take the cake in his hand and stuff it up his nose. Jester didn’t like him, she decided.  
\----------  
Jester excused herself early to prepare herself for Caleb’s arrival. She wanted to really impress him with his first time, so she dressed real fancy. Purple bra with a dark lace around the edge, matching thong layered over a garter set so she could take it off without undoing the garters, thigh high stockings, heels, and a brilliant violet robe that she cinched around her waist. The boy was gonna faint when he saw her.

Caleb came in early. Jester sat him down and sat on the bed, careful to show off a long strip of her thigh as she did so. “So. First things first, Mister Caleb. Boundaries. What should I avoid?”

“I don’t like being tied up,” said Caleb. “No fire, please. No making fun of me or making me do that to you.”

“Sounds good. Undress, please, and sit on that cushion over there.” She got up and strode to her seat at the far side of the room, grabbing her sketchbook.

The ginger man wore a lot of layers. A military coat, a button up shirt, bindings that covered his breasts. Then his pants came off, followed by his underwear, which contained a bundled up sock meant to imitate a cock. Instead of a cock, Caleb had a pretty cunt framed with darker hair. It was very pretty. “Are you gonna draw me?” Caleb asked.

“Yes, I do that with all my clients. It’s how I devote the act to my god, the Traveller. Who’s your god?”

“I follow the Archeart, as does the rest of our house,” said Caleb. He sat down with his knees close to his chest. His legs were covered with a soft, downy fuzz.

“Interesting, considering you all seem human,” said Jester. The Archeart was usually worshipped by elves.

“It was handed down from my mother’s side,” said Caleb. “How did you come to worship the Traveller?”

“He came to me in dreams,” said Jester as she started working on the sketch. “I could always hear his voice from when I was little. But it wasn’t until I was older that I realized who he was.”

Caleb nodded. “Interesting.”

“Yeah, I guess so.” Jester shrugged. She continued on the with the sketch. Caleb had a strong nose, and when his hair wasn’t combed back, it fell into his eyes, and he had tiny freckles all over his nose and cheeks and body. “You’re really pretty, you know.”

“Not as pretty as most,” said Caleb. “Not like Aeodwulf or Astrid. Not like Mollymauk either.”

“You think Mollymauk is pretty?”

“I wouldn’t be marrying them if I didn’t,” joked Caleb. “They’re not just pretty though. They’re stunning. Gorgeous. Radiant as the sun. I’m pretty sure if I looked at them for too long, I’ll go blind.”

Jester laughed. “You got it bad for them.”

“I really do. But they don’t like me.”

“No.” Jester paused in her sketching. “They got a hard-on talking about you.”

“Really?” Caleb furrowed his brow.

“Uh huh. No lie. Promise.”

“Huh.” Caleb rubbed his bottom lip. “You think they really like me?”

“Really. They felt so bad about what they said about your parents.”

“Oh, that?” Caleb shrugged. “I’ve heard worse. I’ve heard people outright say I set the house on fire. Trust me, what he did was just a common mistake.” He sighed and hit his knee. “Verdammt! I should’ve found him, told him everything was alright. Must’ve been embarrassing for him, with me doing that.”

“You should just talk to each other,” said Jester, returning to her sketch.

“Yeah, but talking is hard.”

“It’ll be worth it,” Jester said teasingly.

Caleb groaned. “Ja, I know, I know.” He covered his face with his hands. “Gods, I’ve already messed up so much. We barely talked during the party tonight. Just stood around each other with nothing to say. I abandoned them twice to talk to other people. Then I abandoned them again to go to this appointment. We have no chemistry, we don’t talk...and when we do, one of us always messes it up. The peace between two different houses is resting on this marriage, and at this point, I’m worried we’re all doomed.”

“Don’t say that, Caleb,” said Jester. When she spoke his name, she stretched it out, playing with it like putty. “You’ve only just started. You’ve got a lot of time to figure it out.”

“Not really. Not with all the treaties and deals that are going into this. At this point, we have to figure it out by the wedding or else it will all crumble apart.

Jester nodded. “Maybe you two can come over and visit me! I have a few days where I am free. I should be able to make room for you two. Then we can sit and talk and work things out.” She almost added, “Maybe you two can fuck!” but bit back that particular response.

Caleb nodded. “Maybe. You can give us some tips on how to...do things in bed. Perhaps then our wedding night won’t be such a big open question mark.”

Jester giggled, glad she didn’t have to make the comment for him to get it. “That sounds like fun, yeah. I’m sure Molly will get it. They’re really good in bed.”

“Is he?”

“Yeah,” said Jester. “Really.”

With that, Caleb began to relax. “Okay. What days do you have free?”

“I know I have two appointments coming up. One’s tomorrow and one’s the day after tomorrow. Maybe the day after that? I should be free then, yeah.”

“Okay,” said Caleb. “Okay. That sounds good. I’ll tell Mollymauk tonight.”

“Good,” Jester said proudly. Hopefully, this would all be sorted out before long. Until then, she was happy to help.

After another moment of silence, Jester completed her sketch, showing it to Caleb. He nodded. “You’re a very good artist,” he said, a bit nervous.

“Good. Now get on the bed and let me get undressed, okay?”

“Ja. Okay.” Caleb obeyed, getting up and sitting on the edge of the bed. 

Jester set her sketchbook aside and stepped forward, slowly untying her robe. She let it fall, showing off her lingerie and her body, then did a little twirl and butt wiggle to really show off what she had.

Caleb’s eyes were wide. “Wow. Ja, you are...you are stunning.”

“Thank you, Caleb,” Jester said, before slipping into his lap, arms intertwining around him. “Will this be your first kiss?”

“Nein,” said Caleb. “I’m not totally inexperienced.”

“Well, I’ll try to make it good anyway,” said Jester. She kissed Caleb lightly, gently, then slowly worked up to a lingering kiss. His arms made their way around her, holding her closely. 

“So...what shall we do first?” asked Caleb. He had lipstick smudged all over his lips. Jester wiped it off with her thumb.

“I was thinking I could get into that pretty cunt of yours,” said Jester. “If you don’t mind me calling it that.”

Caleb nodded. “I like it. Sounds nice when you say it.”

Jester smiled and kissed him again. “Alright. Lay back down, please.”

As Jester got up from his lap, Caleb obeyed, laying back and spread his legs. Jester got in between them and slowly dove in, lapping at Caleb’s cunt slowly, getting him acclimated to the sensation. Caleb groaned softly. “That feels really good.”

“It gets better,” said Jester as she paid more attention to his clit.

“Oh, fuck,” said Caleb, twitching slightly. “You were right.” 

Slowly, Jester worked his cunt. Eventually, she took two fingers and slipped them inside him. Caleb squirmed a little, then let out little moans when she rubbed the right spot. Jester pumped her fingers in and out of him, slowly working from two to three, sucking on his clit as she did so. 

“Fuck, Jester,” Caleb said, breath huffy and voice tight. “I’m close, I’m close, I’m--”

In a moment, Caleb came with a gush, filling Jester’s mouth with the taste of his slick. Jester got up and wiped her mouth off, removing the smudged lipstick while she was there. “That feel good?”

“Really good. Is it always like that?”

“It better be,” said Jester. She leaned down and kissed Caleb softly.

“Now, can you show me how to please a woman?” asked Caleb.

“I have another idea.” Jester dug through her nightstand drawer and pulled out a harness with a fake cock on it, made to look like a tiefling’s and painted blue. She held it up. “I was thinking you could learn with this. Since you are going to be sleeping with a tiefling with a cock, after all.”

Caleb nodded. “Will it feel good for you?”

“Yeah! It’s enchanted so that it turns sorta real when I put it on. It’s really cool.”

“Okay then, put it on!” said Caleb.

Jester obeyed, slipping off her panties and slipping on the harness, tightening it and adjusting to the sudden feeling of having a cock. She rubbed it to hardness under her fingers, and it even leaked a little pre-come. “Here. Kneel down before me.” 

Caleb obeyed eagerly, looking up at her with pretty blue eyes -- Mollymauk wasn’t kidding about those.

“Now. Hold the base with your fist. Then start by licking from the bottom to the top. Linger a little at the head.”

He nodded, closed his eyes, and followed her instructions, licking up from the bottom and tracing his tongue along the head.

Moaning slightly, Jester said, “Very good. Now suck the head. Go slowly.”

With a nod, Caleb sucked the head of Jester’s cock, going down a little further than she said, but she wasn’t complaining.

“Good. Look up at me as you do it. People find that very sexy. Start bobbing your head up and down a little. Move your tongue around. Follow the movement with your fist.”

Good thing Caleb was a quick learner. He sucked her cock like he was starving for it. Jester lathered on the praise as he did so, calling him a good boy. She asked if she could pull his hair. He nodded and moaned softly as she pulled it. 

“Faster now. Just a little. You’re doing really good.”

He quickened his pace, getting into the motions and the sucking.

Jester squealed. “Fuck! That’s good. You’re doing really good Caleb -- fuck! I’m getting close, Caleb. Want me to come in your mouth?”

Caleb nodded. 

“Good. Alright.” Jester grunted and came, producing a small puddle of seed Caleb swallowed. She ran her fingers through his hair. “You like that?”

“Ja. That was very fun.” Caleb swallowed, face tightening. “The taste is...very weird.”

“You get used to it,” Jester said. “Now what do you want to do? Want me to fuck you?”

“If you’re willing, ja. That would be nice.”

“Okay,” Jester nodded, rubbing her cock. It was all sensitive post-orgasm, but it was good at bouncing back. “Get back on the bed, please. What position would you like to do?”

“I’d like to face you, please.”

“We’ll do missionary, then.” Once Jester’s cock was hard again, she got in between Caleb’s legs and began to slip into him. He was tight, but she managed to squeeze into him slowly. “Good boy,” she said, holding him close. “You feel really nice. Molly’s gonna enjoy fucking you.”

“You-you think so?” Caleb asked in between slightly panting breaths and soft moans.

“I do,” said Jester. She continued pushing in until she was fully inside of Caleb, moaning softly as she just laid there for a moment, kissing Caleb softly. Then she slowly, carefully, started moving in and out of Caleb, eliciting soft moans from him. “There we go. Good boy.” She petted his hair, carding her fingers through it slowly. “Like it?”

“Mm-hm,” he whined, gaze distant and empty. Jester smiled. If he was this undone, this pliant...she couldn’t imagine him in Molly’s arms, getting fucked by them.

“You’re being very good,” said Jester softly, sweetly.

He nodded. 

“Very good boy,” cooed Jester. She brushed the hair out of his eyes, got a good look at his face. It was a face one could fall in love with, a soft face with a patchy gingery beard and freckles and the bluest eyes Jester had ever seen. No wonder Molly got boners over this guy. Jester felt a little bad for him, that this first moment of him being such a perfect boy was being wasted on someone like her.

She picked up the pace and he groaned, moving his head to the side, leaving his neck bare and open to her.

“Can I leave some marks?”

Caleb paused, then said, “Yes.”

Jester smiled and softly, gently, began to bite and suck at the pale bare skin of his neck, at the freckled skin and the downy hair. Soon there was a pretty red mark on his neck. Jester giggled. It was funny how these things lined up, sometimes. The pair would have their own matching marks, made by her. How oddly perfect.

“That felt...oddly good.”

“I’m glad. I’m sure Molly will give you all sorts of pretty marks to match it.”

“I...I hope they do.”

“I’m sure they will!” She almost said, “They liked marking me,” but scratched that thought, saying instead, “I think it’s a tiefling thing.”

“Hm,” Caleb said. Then he paused. “Can I...rub my clit while you fuck me?”

“You can if you want to.”

Hesitantly, Caleb snaked a hand down, rubbed at the sweet spot. “Okay, that feels good.”

“Doesn’t it?” Jester said, giggling. “It’s my favorite.”

“Ja,” said Caleb, and his sweet little moans became deeper, rougher. Jester quickened. She hit something and he arched his back, toes curling. “Fuck, do that again.”

With a grin, Jester repeated the motion, a sharp thrust in, hard and deep. He practically cried out in pleasure. “You like that?”

 

“Gods, that’s fantastic.”

“I’ll take that as a yes,” said Jester. She giggled and kept on doing it, kept repeating that movement. Every time she did, he gasped and moaned and cried out. His legs wrapped around her hips, keeping her close as she thrust into him. “Fuck, you feel really good, Caleb.”

“Danke,” he muttered, gasping.

“I might be pretty close,” said Jester.

Caleb nodded. “Close.”

She kept on thrusting into him, kept on fucking him until she felt him clench and cry out. As soon as she felt it, she pulled out and rubbed her cock until it finished on his stomach. “Fuck,” she said, exhausted, before laying down and cuddling up next to him. “Was that good?”

“Good doesn’t quite cover it,” said Caleb. “Amazing, maybe. Stupendous. Awe-inspiring.”

Jester giggled. “Thank you, Caleb,” she said, arms wrapping around him, kissing him. “I’m proud of you. You’re gonna do great with Molly.”

“You think so?” he asked. “Think we can make it work.”

“At the very least, you’ll have really great sex.”

“Ja, I hope so,” said Caleb with a rare smile. Gods, no wonder Molly liked him so much. 

“Want to go downstairs? Have some tea?” Jester asked. She sat up and got the towel, cleaning off his belly.

“That’d be nice, ja,” said Caleb.

“Okay!” Jester got her robe from the floor and handed Caleb one, a blue one of hers that matched her eyes. He wrapped himself up in it and followed her downstairs, where they sat and got their tea and cakes.

While they were there, Molly arrived. Jester waved him down and invited them to join them. Molly did, and they talked. 

“Oh, Mollymauk,” said Caleb, a bit nervously. Jester watched him, knowing what he was going to say. “Jester offered to help us, and I was wondering--” His gaze was distracted though, and his head cocked. “Who’s that with Trent?” he asked, pointing to the distance. 

Mister Ikithon was with a Tabaxi woman in maroon robes. She came up to Molly and slapped them across the face. Caleb and Jester both stood, both sharply said, “Hey!” at her, but she seemed unfazed by their presence. “Lucien,” she said, enraged, “what in the nine hells are you doing here?”

Molly shook their head. “I don’t know a Lucien,” they said, eyes darting everywhere. “You must be mistaken.”

“I am not,” she insisted. “I know my fiance when I see him.”

“Fiance?” Caleb asked, shocked.

“Yes. And who are you?” the woman asked.

“His fiance,” said Caleb.

“I’m terribly sorry, Caleb,” said Molly. “But I don’t know who this is.”

“What do you mean, you don’t know who I am?” asked the woman, furious. “You were my fiance, you left me two years ago, you’ve disappeared ever since, and now you reappear and say you’re some man named Mollymauk?”

“I’m not a man!” said Molly, furious. “Stop calling me that! And I’m sorry, I don’t know who you are. I don’t have a good memory. My past is...it’s gone, before two years ago. If I am this Lucien, then I’m not him, now. I’m sorry.”

The woman scoffed and stormed off. Mister Ikithon gave Caleb a stern look, a look that said, “I told you so,” and turned on his heels, following the woman out.

Molly shook their head. “I’m sorry about that. I’m...I’m going to bed. Caleb, I’ll see you in the morning.”

“Mollymauk, wait--” Caleb said, but Molly walked off before he could speak. Caleb followed him, giving a last look of apology to Jester, leaving her alone with the tea set and the cake crumbs.


	4. black scales, blue velvet

**Summary for the Chapter:**

> Content Warning for Sexual Assault discussion. Didn't go deep into it, but I hinted at it in the dialogue and the character has scars from it.

Marian proposed a ladies’ night with the brides of the bunch, and Jester was shoved into hosting it. Beau was disinvited (fortunately for her; she told Jester she’d rather stick daggers in her eyes than sit around a table sipping tea and pretending to moon over her fiancee) and Orion and Molly were considered feminine enough to be included. So Jester sat around a table with Astrid, Orion, Calianna, and Molly, four relative strangers with not much to talk about except their future partners.

What a set-up for success, Mama, Jester thought.

They were civil enough at least. Astrid was very polite, but she had a cunning sharpness to her that Jester didn’t trust. Orion and Calianna were both absolute sweethearts, and Molly was Molly, and they fit well anywhere. Soon enough the conversation started without Jester nudging it -- Astrid and Orion talked about Aeodwulf and her adventures with him as a youth, and Molly listened as Cali bragged about her new fiance.

“They’re really sweet and they make me tea every morning and we sit in the gardens and they take me on walks and they’ve been very romantic. I’m quite happy with them. What about you? You and Caleb getting along well.”

Molly went blank. “Well. I kind of forgot to tell him I’m an amnesiac? So someone from my past came about, embarrassed me in front of him, then left, so...that was a bit of a mess.”

“Oh dear,” said Cali. “Did he at least comfort you after all that?”

They sighed. “I kind of pushed him away? I don’t know. I just wanted to be left alone.”

“Aw. Well are you feeling better now?” asked Cali, patting his arm.

“Yes, yes I am,” said Molly. “Much better than I was last night, that’s for sure. What did you and Caduceus get up to last night?”

Cali smiled. “Well. We had a bit of time to ourselves.”

“Oh?” Jester raised an eyebrow.

“Yeah. It was...pretty amazing.”

Jester giggled and laughed. “Good for you!’”

“Question. Are they as big as they say?”

For a moment, Cali paused, head cocked in confusion, but then she nodded. “Yes. Yes, they are.”

Molly smiled. “Nice.”  
\-----------  
It was to Jester’s surprise that Cali was her client for the night. She came up in a draped green dress that showed the gentle curve of her thin form. The fabric matched the ribbons braided in her hair. Jester sat up a little when she saw her. “Hello. Sit down, please.”

Cali smoothed her dress and sat down, prim and proper.

“I didn’t expect to see you here.”

“Really?” Cali cocked her head to the side. 

“Yeah. You didn’t seem to be the type who’d want my services.

“I guess so.” She shrugged. “Right now I just...need to get out of my head for a while.”

“That’s a fair thing to want.” Jester smiled at her warmly. She was really lovely in this light. “Now. What do you want to me to avoid?”

“I don’t like knives. Or blood.”

“That’s fair. That all?”

She shrugged. “All I can think of right now.”

Jester nodded. “Okay. Undress and sit down over there.”

“Why?” Cali asked. “You got some sort of ceremony or something?” She seemed...oddly nervous. Jester thought it was odd.

“Oh, I just draw you,” said Jester. “I make paintings of all of my clients. It’s my offering to the Traveller.” Jester got up and adjusted her lacy bodice, squishing up her boobs a little.

“Ah. Okay, that’s fine.” She got up and undressed, brushed her hair out of her eyes. In doing so, she revealed the pretty black scales that travelled up and down her right side. It was...stunning. Jester was frozen in place for a moment.

“Wow. You’re...really pretty, Cali.” She blinked. What was wrong with her? It was like she was glued to the floor.

“Why, thank you, Miss Jester!” said Cali, sitting down, tail falling to her side and hugging close to her leg. She played with it a little as she sat there. “You gonna draw my picture?” Cali asked after the awkward pause dragged a bit too long.

Jester blinked away the haze. “Sorry! Sorry. Got a little...dazed.” That wasn’t it. This was different. She sat down in her chair across from Cali, blue velvet robe slipping off her shoulder. She started drawing Cali. “So. What brings you here? I thought you were really happy with your fiance.”

“Oh. Yeah. That.” Cali ducked her head guiltily. “I mean, I had arranged for this ahead of time, but...now that I think about it, I think I need someone to talk to.”

“About what?” Jester asked.

Cali sighed. “Have you heard about what happened with me? How I came to be head of House Draconae?”

“I heard there was a thing with dragons,” said Jester, “but that goes without saying a little.”

“Yeah,” Cali said. “You see, Port Damali and House Draconae were ruled by this...cult. They worshipped this traitor goddess, the mother of all dragons. And apparently they had some sort of chosen one, someone who was part dragon, who was going to be this big deal...and that was me, apparently.”

“Wow. Lucky you.”

“Yeah. Real lucky. I went from an orphan who was probably gonna be left out on the streets to starve, or worse, to...someone really important. Someone worshipped. Someone special. But it was all a hoax. The cult was really bad. They did bad things, made me do bad things.”

 

“What kind of bad things?”

She paused, hesitantly. “We killed people.” Her face got all somber and serious. “I killed people.”

“Ah.”

“Yeah. I realized that the cult was doing terrible things and I put a stop to them. But after they were all executed, I was left alone. Without me, House Draconae would’ve been taken over, renamed, maybe even conquered by some of our neighbors. It would’ve been awful for my people. So I’m still here.”

“I’m sorry you went through that,” Jester said. She set aside her notebook and came over to hug Cali, who had tears in her eyes.”

“Thank you,” said Cali.

“It’s okay,” said Jester. After Cali calmed down, Jester said, “Now where were you going with this?”

“Well, it’s just that...I haven’t told Caduceus about this?”

“Why not?” asked Jester, eyebrows scrunched up.

“I don’t want to burden them with it. It’s unfair to them. They don’t deserve to deal with my trouble.”

Jester nodded, but said firmly, “Sooner or later, they’ll know. It’s better that they know sooner instead of later.”

“I know.” Cali buried her face in her hands. “But talking about it is hard. I don’t want them to see me any differently because of this.”

“I don’t see you any differently.” Jester smiled at Cali, brushing aside her hair to look her in the eyes. “You’re still really sweet, and really nice, and really, really pretty. I’m sure Caduceus will see the same Cali when they hear what happened.”

Cali nodded. “Thank you, Miss Jester. That means a lot.”

“You don’t have to call me miss,” said Jester. “You know that, right?”

“I like calling you miss.” Cali smiled. “It’s polite.”

“Alright, if you want.” Jester’s tail lashed slightly in the air. She looked into Cali’s eyes and felt herself slip from thoughts. She really, really wanted to kiss her right about now. But she blinked. What was going on? This was really different than what she normally did. “Well. Let me get back to drawing you.”

“Oh. Oh yeah. Sorry about that.”

“No! It’s no problem!” Jester smiled and kissed Cali on the forehead. She’d give herself that. As she sat back down in her chair, Cali smiled warmly at her. Jester then lost herself in the drawing. Normally she did a really rough sketch, not many details, enough to know what she was painting when she got to it, but this time...this time she worked really hard to make it perfect. She redrew Cali’s nose a million times, trying to get the perfect angle just right. Jester tried desperately to capture the scrunching of her eyes and and bumps of her scales and the way her hair framed her face so prettily. It wasn’t until she had a damn near perfect drawing that she realized she’d wasted a lot of time doing this. “Shit! I’m so sorry. I normally just do a little sketch but. I kind of got carried away.”

“It’s okay,” said Cali, a bit tiredly. “It was nice, watching you work.”

“Was it?” she asked.

Cali nodded. “Yeah. Can I see it?”

“Sure!” said Jester. She showed her the picture.

Cali’s mouth dropped. “It’s so beautiful, Miss Jester. You’re a really good artist. Wow. I’ve had a lot of portraits done before but I’ve never had any that were done like this. Thank you.”

Jester smiled, glad she really liked it. “Thank you, Cali.” She set aside the drawing. “Now that that’s done, we can get to what you’re actually paying me for. Why don’t you sit on the bed while I get undressed, hm?”

“I can do that,” said Cali, and she got up and sat down on the bed. 

Jester followed her towards the bed, slipping off her robe and starting to undo her bodice. It took a minute of trying to untangle the knot at the bottom that she remembered that Nadine had laced her bodice, and Nadine always used a damn knot Jester couldn’t untie from behind. She cursed and said, “I’m sorry, Cali, but can you untie this? I can’t do it from here.”

“Sure!” said Cali. She made room for Jester on the bed and Jester sat down by her. Cali bent down at an awkward angle but managed to undo the knot. “Want me to get you out of this?” she asked.

Normally, Jester would’ve said now, but right now all she wanted was Cali’s hands all over her, so she nodded and said, “Sure.”

With lithe and steady hands, Cali undid the bodice, pulling the thing over Jester’s head when there was enough room to do so. When she saw Jester’s body, Cali stopped, eyes wide. “Miss Jester...you’re so pretty.”

Blushing, Jester smiled and said, “Not as pretty as you.”

The two women grinned at each other, and as silence fell, Jester realized how much she wanted Cali. She leaned in and kissed her. As she did, she pulled Cali close and explored her chest with her hands, feeling over her skin and scales. Cali did the same, grabbing at Jester’s breasts and stroking at the stretch marks and fat rolls of her tummy. When they pulled apart, Cali said, “That was really nice, Miss Jester,” then pulled her on top of her for a second kiss.

Jester’s hands started moving down lower, lower, grabbing at Cali’s sides, her hips, her ass. One rubbed at where she expected a cunt to be, but she only found bumpy scales. Jester checked out her partner properly for the first time, a bit confused. There was a clit, yes, with ridged plates black as the surrounding scales. But there was no cunt underneath it, just scales that were scarred over. Jester looked up at Cali, confusion clear on her face.

“Oh! Yeah. It’s draconic down there. Just rub my clit, and it should fan out.” Cali shifted to give Jester better access to her clit.

“It’s all bumpy,” said Jester, still befuddled. “It’s not like the rest of your scales.” It was odd and irregular and dented inwards. She could tell it was damaged somehow. “Can I ask what happened?”

Cali sighed. “It’s...not entirely pleasant.”

“You don’t have to tell me if you don’t want to.”

“Yeah, but I ought to. I’ve never told anyone. Not even Caduceus.”

Jester pressed her cheek into Cali’s thigh.

“I’ll just say that members of the cult decided that I should offer them much more than sacrifices,” she said somberly. “And they didn’t let confusion over my anatomy get in their way. At least, until I really started screaming.”

“Oh, you poor thing.” Jester climbed up and held Cali close, petting her hair. They stayed like that for a while, legs intertwined, while Cali sniffled and Jester peppered her with kisses. “Are you okay to continue?”

“Yeah, I’m fine. Just be gentle. It usually hurts if you try to force it.”

“Okay.” Jester nodded and slipped down between Cali’s legs again. She gently kissed the bumps and dents over her cunt, then lapped at her clit. Cali’s breath halted. Jester kept an eye on her to make sure everything was okay while she licked and sucked at her clit. Slowly, the ridges became softer, more separated, as the clit grew erect. Meanwhile, the scales of her cunt opened up, fanning out. Some of the scales were a bit crooked, but they still opened, revealing a smooth, wet cunt that made Jester’s mouth water. “Let me get something for you.” She originally reached for the first drawer of her bedside table, but instead reached for the second, going for her personal stash. She pulled out a thick, rodlike device with a button that clicked on, making the thing buzz. “I only use this on myself normally...but I want to make an exception for you.”

“Oh, you don’t have to do that!” Cali said.

Jester shook her head. “I want to.” She pulled Cali into her lap, wrapping one arm around her back to hold her, while the other hand navigated the device to her clit, pressing it lightly against it. It was at the lowest setting of vibrations for now, but even then, it made Cali moan softly.

“That feels really good, Miss Jester,” she said, a bit shyly.

“You like it?”

Cali nodded. 

Jester pressed kisses to her forehead. Slowly, she slipped the wand into Cali’s cunt. “You like that?”

“Mmhm,” said Cali, biting her lip.

Slowly, carefully Jester pumped the wand in and out. “You’re doing very well,” she said gently.

“Thank you,” Cali said. “This feels really good.”

“I’m glad.” Jester watched as Cali moaned more. She alternated between pumping the wand in and out of Cali’s cunt and pressing it against her clit. Eventually, when Cali had been good, moaning so prettily in Jester’s arms. Jester asked, “Want me to turn up the vibrations?”

“Please,” Cali whined, nodding.

“Good girl, wanting this so bad.” Jester pressed the button and brought the vibrations up. The buzzing intensified. “You like that?” Jester pressed it against Cali’s clit, and Cali pressed back against it.

“Yeah,” Cali said, all breathy and weak.

“It’s not even close to being all the way up,” said Jester. “When it is, you’re going to be a mess.”

Cali nodded, giggling. “Yeah. This feels really good.”

“Well, you’re taking it very well,” said Jester. She slipped it into her again, fucking her gently with it. “I wonder how many times I can make you come before it’s all the way up?”

“Probably a lot,” Cali said, smiling.

“Want me to try?”

“Uh huh,” Cali whimpered.

Jester smiled and fucked her with the wand properly, making an obscene squishing sound as she did so. When Cali’s moans escalated, she took the wand and pressed it hard against her clit. Cali pressed back against it, whining and whimpering. Jester slipped the wand back in and pressed against her upper walls, seeking the spot that would make her go wild. Cali began to squirm, and Jester gently fucked her, rubbing that spot.

“I’m close, Miss Jester,” Cali said, whimpering.

“Come for me, darling,” said Jester, kissing Cali’s forehead.

Cali cried out, body twitching, draconic claw reaching down and ripping the sheets. Jester turned up the intensity just as she came, keeping it inside of her. When she slipped it out, the scales closed, and Cali winced a little. 

“We’re not even done yet. You want to keep going?”

“Please,” Cali begged.

Gently, Jester pressed the wand against Cali’s clit until her scales started fanning out again. Then she once again alternated between fucking her with the toy and pressing it against her clit. “You’re so pretty like this,” she said, holding her gently.

“Th-thank you,” said Cali weakly. Jester turned up the vibrations, and she moaned.

“You sound pretty, too,” she said. Cali wriggled in her arms, desperate to feel the vibrations. “We’re getting close to the most intense one...but I wanna hear you beg for it first.”

“Gods, please,” she said weakly.

“I need more than that, sweetheart.”

“Miss Jester, please turn it all the way up,” she said. “I need it. Please.”

“Beg a little more and you might get it.” She pressed the wand hard against Cali’s clit. Her back arched as she gasped.

Whimpering, Cali begged, “Please, please, please, Miss Jester, I need it, I’m so close, please, please.”

Jester smiled and clicked the button, rubbing the wand against Cali’s clit. Cali gasped, crying out, moaning. She came, gushing a little onto Jester’s thigh. “Good girl,” Jester said. “Very good girl.”

Cali nodded, tired. “That was really nice, Miss Jester,” said Cali. She reached up and pulled Jester in for a kiss. Jester clicked off the wand and set it aside, holding her. “Now it’s your turn,” Cali said.

“You don’t have to,” said Jester. “I know you’re tired.”

“But I want to,” said Cali. “I want you to come, too.”

“Okay.” Jester nodded. “How do you want to make me come?”

“Do you have any toys I can use on you?” Cali asked.

Jester nodded and reached back down in her personal stash, grabbing a toy with a flared base and handle and a bottle of oil. “Can you fuck my ass with this?” she asked. 

“Sure,” said Cali. She stretched out her legs and pulled Jester into her lap, slipping off her panties and setting them aside. She oiled up Jester’s ass and the toy, before slowly, carefully, slipping it in.

“Oooh, that feels good,” she said. It had been a while since she’d had anything up her ass, so the stretch and pain were delicious. 

“Like it?” asked Cali. She brushed her hand through Jester’s hair, tucking the rogue strands behind her ear. 

“I do,” said Jester.

“I’ve never had anything up there.” Cali began to move the dildo in and out.

“It’s amazing,” said Jester.

Cali nodded and continued to fuck Jester with the dildo, slowly picking up speed. Jester moaned and mewled in her lap, her body slowly acclimating to the feeling of getting fucked in the ass. 

“You know what would be even more amazing?” she asked.

“What?”

“If we used the vibrating one at the same time.”

“Alright.” Cali handed her the wand, and Jester turned it on to its full intensity, pressing it to her clit. 

“Fuck!” Jester moaned as she rubbed herself on the wand. Cali fucked her faster.

“Good girl,” said Cali. “You like that?”

“I like it a lot -- fuck!” Cali had hit a sweet spot, and Jester was close. “I’m gonna come! Fuck!”

“Come for me, Miss Jester,” said Cali. 

Jester eagerly obeyed, bucking and gushing in Cali’s lap.

“That was really nice to watch,” said Cali, giggling slightly.

“It was really nice to feel,” said Jester. She turned off the wand and let Cali take out the dildo. When they were tossed aside, Jester rolled over to her back and pulled Cali on top of her, kissing her deeply. They kissed for a good while, hands wandering over each other’s bodies. After a while, Jester pulled away. “It’s getting late. You should probably head to bed.”

“Oh,” said Cali. “I thought I slept over with you.”

“Well...we’re not supposed to. But if you’re really tired...I might make an exception for you.” 

“Only if you want to!” said Cali. “I don’t wanna take up any space or anything.”

“No...I think it would be nice.” She hadn’t shared a bed since...damn, since forever. “It’s nice to sleep with someone but it’s really nice to actually sleep with someone.”

“Yeah, I know!” said Cali. “Want me to clear the bed for you?”

“You don’t have to,” said Jester, picking up the toys and setting them aside. They’d be washed in the morning.

“Well, I want to help!” She noticed the tears in the sheets that her claws had made. “Oh, dear...I’m awfully sorry. I didn’t mean to ruin your sheets.”

“It’s okay,” said Jester. “We’ll leave it for tonight. Sheets are sheets.”

“Okay,” said Cali.

Jester got up and turned off all the lights in the room and grabbed a blanket from beneath the bed, snuggling up next to Cali under the covers. “Thank you for such a wonderful night,” she said.

“I should be thanking you, Miss Jester,” said Cali.

“Fine. You’re welcome.” Jester wrapped her arms around Cali and slowly fell asleep.  
\----------  
Slowly, Jester woke up the next day, surprised to find Cali in her bed. They were holding each other, faces close enough to kiss. But Jester didn’t kiss her. Instead, she watched Cali’s face as she slept, surprised to see how beautiful she was. In this perfect little moment, Jester realized something. 

She was catching feelings.

Oh, dear.

It was the weakness of the Lavorre family, she supposed. It had happened to her mother, and now it was happening to her. Jester knew she should stop it. There were so many reasons why this was a bad idea. Jester was a prostitute! Cali was getting married! They were strangers who were probably rarely going to meet after this. It was a bad, terrible idea.

So she asked the Traveller what she should do.

She could feel his presence, all warm and nice. Quietly, as to not wake up Cali, she whispered, “What should I do? I know I need to stop this. But the idea of her leaving...it hurts.”

“Let the heart want what it wants,” said the Traveller with his gentle voice.

“But what do I do?”

“Follow your heart. It will lead you to where you need to go.”

Jester scrunched up her face, confused. “But she’s leaving!”

“Whoever said you’d be staying here?”

The idea of leaving Nicodranas hurt. But she breathed in deep and she trusted. “Okay. I will follow my heart. Thank you, Traveller.”

“You’re welcome, dearest.” And the presence left her.

Sweetly, Jester woke up Cali with kisses. “Come on, Cali. You have a busy day today.”


	5. two tails, pink and blue

Cali invited Jester to come with her to finish dress fitting. Jester had never been to one herself, but she had expected people there, a family, someone. But the only people there were Cali, Caduceus, and Jester.

Despite the lack of people, the room was filled with conversation. Jester paid for a bottle of champagne, and the group laughed and chatted as Cali was fitted and fussed over. When she showed off the finished dress, Jester felt her heart drop. She was stunning. The dress was made of green velvet. It had a sleeve on her left arm, and her right side was bared, showing off her gorgeous black scales. It flowed down simply down one side, trailing into a long train. Her veil was made of dark green lace so dark it was almost black. She looked gorgeous. Jester drank her champagne, hoping to drive out the heartsickness.

Meanwhile, Caduceus’s eyes were wide with love. They were clearly head over heels, watching her every graceful move with adoration. Somehow, this made things even worse. How could she interrupt this happy relationship with her own feelings? She tried to be happy, but gods, this stung.

Then it was Caduceus’s turn to be fitted. They wore a robe made out of sky blue material that was meticulously embroidered with flowers and butterflies all along the bottom. They twirled around and let the thin gauzy fabric dance in the air. Cali clapped and watched eagerly, while Jester sat in her little bubble of sadness. Gods, she felt stupid and selfish.  
\-----------  
Jester was surprised by who her client was for the second day in a row. Caduceus came into the room wearing fine robes of material so sheer she could see the patches of pink fur over his grey fur. They smiled and said, “Hello, Jester. I believe I have an appointment with you.”

“Yes, you do,” said Jester. She wanted to call this off, to stop things before her jealousy ruined things. But then they smiled at her and she couldn’t, she just couldn’t. “Sit, please.”

Caduceus nodded and obeyed. 

“So. First of all. Do you have any things you don’t want me to do? Any boundaries you don’t want to be crossed?”

“I don’t like being called names,” said Caduceus. “Other than that, I can’t really say.”

“Okay. Undress and sit over there, please.” Jester stood and showed Caduceus where to sit.

They smiled and undid their robe. Underneath they were...wow. They had a broad, lithe form covered in downy fur and tufts of pink on their chest and around what had to be the hugest cock she’d ever seen. They wore a pretty corset with pink flowers all around it. “Would you mind helping me undo this?” Caduceus asked. “I always have problems with untying these.”

Jester nodded. “Of course.” She stood behind Caduceus, untying the corset with shaking hands. Underneath the corset they were...wow. They had soft muscle and more pink fur all around their belly button. It was quite lovely. “You look lovely,” she said.

“Thank you,” said Caduceus. “You’re quite lovely yourself.”

She blushed. This shouldn’t be affecting her this much...but it is. Jester set the corset aside and the two sat down in their respective seats. They sat cross-legged, in a sort of meditative pose.

“So,” said Caduceus, “you draw?”

“Yes.” Jester sketched out their pose.

“How long have you been drawing for?”

“Since I could hold a pencil, I’ve been drawing,” said Jester. “At least, that’s what Mama says.”

“Ah.” Caduceus nodded. “So you’re good?”

“That’s what a lot of people say,” said Jester with a shrug.

“Hm.” There was a slight lull in the conversation. Then Caduceus asked, “Cali told me she visited you. Did you draw her?”

“Mmhm,” said Jester. “Would you like to see it?” Normally she didn’t show her sketches to anyone except her subjects, but she could make an exception for Cali’s fiance.

Caduceus nodded and leaned forward, and Jester flipped back to the page with the sketch. “Wow,” they said, amazed. They tucked a lock of pink hair behind their ear. “It’s beautiful.”

“Thank you.” Jester flipped back to the page with their sketch and continued. She got a bit lost in the drawing again. Jester really had to stop doing this, but she just couldn’t help it. The texture of their fur, the softness of the nose, the flow of their hair, the soft muscles...it was all too lovely not to capture. Once again, her sketch was more complete than usual. Once again, she had wasted time.

She showed Caduceus the sketch and they smiled, making Jester’s heart skip a beat. “It’s beautiful,” they said. “Never been sketched before, you know.”

“Really?” asked Jester.

“No. I know most families do those big portraits, but we don’t, really. It’s one of those traditions that never stuck with our family.” They shrugged.

“I’ll have to show you my painting when it’s done,” said Jester. “I’m going to work on it tomorrow. You and Cali should come if you can. Keep me company.” Normally she didn’t invite people to watch her paint -- it was a private affair, a chance to meditate and worship and thank her god -- but she was sure the Traveller wouldn’t mind. She was following her heart.

Caduceus smiled once again. “I’d love to, and I’m sure Cali would as well.” They paused for a moment. “She sang your praises today, you know.”

“Really?”

“Yes. I knew I wanted to come and see you before, but now she’s got me excited.”

“Oh, thank you,” said Jester. She set aside her sketchbook. “And tell Cali I said thank you for the fine praise.”

“I will.” Jester stood, looming over Caduceus for the first time. “Shall we?”

Their eyebrows raised as they looked her up and down, taking in the beautiful figure. They smiled. “Yes, ma’am.”

Jester grinned. Oh, they were in this sort of mood, huh? She liked being in charge. “Sit down on the bed. Keep your hands by your sides. No touching. Okay?”

“Yes, ma’am,” said Caduceus. They sat down on the bed, soft ear perked up a bit.

“Good pet,” said Jester. They beamed. Jester felt her heart thud. “You like being called pet?”

They nodded. “Very much so, ma’am.”

“I’m glad. I’m going to be calling you that a lot tonight.” She undressed, taking off her robe and the lacy lingerie. While she wanted to jump their bones right at that second -- their cock was starting to harden at the sight of her -- Jester restrained herself and asked, “Are you into being tied up?”

“I’ve never tried it,” said Caduceus.

“Hm. Okay. You’ll have to let me know if it’s too much, okay?”

Caduceus nodded. “Yes, ma’am.”

Jester smiled. “Good pet.” She went to go get the rope from one of her dressers. She had them in all sorts of colors and lengths. She got two pairs of shorter ones, the silk ones that were really soft, in two different shades of pink. One was a darker shade of tulip pink that matched her lipstick, and the other was a softer pink that matched their hair. Jester turned and asked, “Which color do you like better dear pet?”

“I like the lighter shade better, ma’am.”

“Good pet. I like it, too. Matches your hair.” She put away the darker ropes and moved towards the bed. “Put your hands on the headboard, palm up, please,” she said.

“Yes, ma’am.” Caduceus obeyed. 

She tied their soft paws to the headboard, running two fingers underneath the ropes to make sure it wasn’t too tight. “That good, dear pet?”

“Very, ma’am. Though, may I ask for some pillows to support my head?”

“Of course, pet.” Jester stacked pillows under their head, making sure they were nice and comfortable. “This good?”

“Yes, ma’am,” said Caduceus.

“Good.” Jester moved toward’s Caduceus’s legs, noticing how hard their cock was. “You’re so hard for me already!” she giggled. “Are you excited for me?”

Caduceus nodded.

Jester smiled. “Good pet.” She moved the chair next to the bed over to in front of the bed and went searching through her personal toys. “Now, pet, you’ll have to prove how good you are.” She took out one of her big dildos, a half-orc cock, and sat down on the chair, spreading her legs.

They put two and two together and sat up a bit straighter. “Yes, ma’am. I’ll be good.”

“If you’re very good and watch me come without wriggling or begging, I’ll suck your dick. That sound good?”

“Yes, ma’am.”

“Good.” Jester slowly slid the head of the half-orc cock in, pumping it a bit. It didn’t quite reach that inner spot, but it felt good and made a nice, obscene sound she just loved. 

Caduceus was fully hard now, and gods, they had a pretty cock. A nice swollen knot and bumps along the shaft, a pretty petalled head. It was long, too, easily the biggest cock Jester had ever seen, and that was saying something. She understood why Cali was impressed. 

Jester slid the first bump of the dildo into her cunt, moaning. She spread the lips of her vulva out and angled her hips upward so they had a clear view of it stretching out her cunt. “See how well I can take big cocks?” asked Jester, smiling. “This is how easily I’m going to take your knot.”

They whined a little, breath panting in anticipation.

She stopped, raising her eyebrows. “Uh uh, pet. No whining. You gotta be patient, alright little pet?”

“Yes, ma’am. Sorry.”

“Sorry for what?”

“Sorry for whining, ma’am?”

Pumping the cock in her cunt, Jester moaned as she said, “Good pet.” The ridge rubbed right on the spot in her that made her body light up. “Fuck. You like watching me fuck myself?”

Nodding, Caduceus said, “Yes, ma’am.”

“You like watching me take this huge cock right in front of you? Even though I’m not fucking yours?”

“Mmhm.”

“Use your words, pet.”

“Yes, ma’am. I like it very much.”

“Good pet.” Jester closed her eyes, imagining Caduceus fucking her. It was a good image. The second ridge slid in, and she was so full. She fucked herself properly, making slick sounds that filled the room along with her moans. In between thrusts of the cock, she rubbed her clit, intent on making herself come. “Oh, Caduceus,” she moaned. “You good little pet. You must wish you could rub your cock to this. Don’t you? Don’t you want to fuck your cock with your hand?”

“Yes, ma’am.” Their voice was a little whiny, but before Jester could comment on it, they said, “Sorry for whining, ma’am.”

“Good pet. You make it so easy-- fuck!” She had hit that spot hard, and now she was close, so close. She pumped the cock fast, rubbing her clit hard, and her back arched and her toes curled and her head threw back and, “Fuck, fuck, fuck, fuck!” Jester screamed. As the orgasm passed, she slipped out the cock and let him watch her pussy gape for a moment. “You like that little show?”

They nodded. “Yes, ma’am!”

“You must want my cunt more than anything, don’t you?”

“Yes, ma’am, I do!”

Jester giggled. “Not yet, sweet pet. You were very good watching me, but you haven’t earned the right to my pussy just yet. You’re gonna have to work properly to earn that.” She set the cock aside and knelt at Caduceus’s feet. “But I am gonna suck your dick. That sound good?”

“That sounds very good, ma’am,” said Caduceus.

“I’m glad.” She used their pre-come as lube for her hand, rubbing it up and down their length. Then she licked up and down their cock, feeling all the bumps and the little ridge beneath the head and the cracks of the petals and that pretty, pretty knot. After a while of teasing, she slipped her mouth over their head, using her fist to rub what she couldn’t fit.

Caduceus moaned. “That feels really nice, ma’am,” they said a bit weakly.

“You like it when I suck your cock, little pet?” asked Jester, rubbing their shaft using her spit as lube. “You like it when I touch you.”

“Yes, ma’am,” they said quietly.

“I can’t hear you,” Jester said in a sing-song voice.

“Ma’am, I really like it when you suck my cock,” they said, a bit louder.

“Louder. I want to hear you really clearly.”

“Gods, ma’am,” Caduceus said, bucking his hips slightly. “I really like it when you suck my cock!”

“Good pet,” Jester said before returning to suck their cock with fervor. She bobbed her head up and down quickly, pumping their cock with her hand, while she slid her free hand down to rub her clit. Her moans vibrated on their cock, eliciting more moans from him.

“Ma’am, I’m close,” they said.

At that point, Jester stopped, removing her mouth and hand from their cock. They whined, but she said, “Uh-uh. Good pets earn the right to come.” She climbed up on the bed, towards their head. “Speaking of earning…” She straddled their face, plastering her cunt over their tongue.

And, fuck, what a tongue it was. It was wide and broad and long, and it swiped over her cunt with fervor. Jester moaned and wriggled as their sucked at her clit, shoved their tongue into her pussy, licked at her lips. She cried and moaned and bucked and screamed with pleasure until they sharply sucked her clit from a long, long second and wrenched an orgasm out of her, then another right on its heels. She was already fucked out, but she wanted more, needed more, so she moved towards his cock and began to slide it into her cunt.

“Fuck,” she moaned. She’d never fucked a firbolg before, but she had heard tales and damn, they were all true. It felt divine inside her, better than any cock she’d ever felt. “Oh, good pet,” she groaned, before moving up and down. The bumps were spectacular, the head bumped at that spot and brought moan after moan from her. “Fuck, Caduceus. You feel so good inside of me.”

“Thank you, ma’am,” they said in between moans.

“You like being inside of me?” she asked. “You like having your cock buried in my -- ah, fuck! -- in my pretty cunt?”

Caduceus nodded. “I love it, ma’am. You feel so incredible.”

“Oh, good pet. Very good pet.” Jester rubbed her cunt, already so close with their cock inside of her. “Fuck, I’m going to come. Fuck. Fuck!” Her voice got all squeaky and high and then again she came, dissolving into their chest. “Fuck. You’re wearing me out.” She sat up, untying his hands. “Why don’t you take control a bit and fuck me. If you get me to come one more time I’ll let you come inside of me. I wanna take that knot so bad.”

“Yes, ma’am.” As soon as their hands were free, they flipped Jester onto her back, fucking into her, making slick, obscene sounds as they both moaned and cried out. They kissed for the first time, kissed passionately, tongues colliding with each other. One of their thumbs went to her clit, rubbing it fast, exactly the way she liked. 

“Fuck!” she said, before coming again. Gods, with them she was like an orgasm machine. “Good pet. Good, good pet. Now come. Come inside me.”

It didn’t take long. Easily, they slipped their knot inside of her, and easily, they came, pouring wave after wave of come inside of her until it was pouring out. They collapsed on top of her. 

Jester smiled, brushing their hair out of their eyes. “Was that fun?” Caduceus asked.

“Yeah,” they said. “It was.”

“Do you think Cali would mind if you stayed in my bed tonight?”

“I think she’d be fine with it. She stayed with you last night.”

“Good,” she said. “Very good.”


	6. oils paints on blue skin

In the morning before everyone else was up, Jester and her mother took tea together. The red tiefling noticed her daughter bring a small blue bottle filled with dark liquid. “You let someone finish inside of you?” asked Marian. “You’re normally so careful.”

Jester shrugged. “Special occasion, I guess,” she said, trying to sound casual. She drained the bottle, making a face. It tasted awful.

Marian raised an eyebrow. “You have to be more careful darling. That tonic doesn’t always work.”

“It’ll work,” said Jester. “I trust it.”

Someone approached their table. It was Caleb, harried and unshaven. “Hallo, Jester, Madam Lavorre.” He bowed slightly and turned towards Jester. “Are you free tonight? I’d like to make a bit of a last-minute appointment.”

“Certainly,” said Jester. “For just you?”

Caleb shook his head. “Nein. For me and Molly. They...haven’t spoken to me since the incident with the strange woman. I fear he may call the wedding off if I don’t talk to him.”

“Oh no,” Jester said. “I’ll get an appointment for you two, right away. Will you want me to invite him to my room or do you want to do that?”

“If you could? If he gets the invitation from me, he might reject it.”

“Alright. Consider it done. I will see you this evening.” Jester smiled and patted his arm before he left.

When he left, Marian gave her daughter a suspicious look.

“Not him, no. He doesn’t have the...parts for that.”

“Ah.” Marian nodded. “Mx. Tealeaf? Is that what this fuss is about?”

“No, not them.” There was fuss with them, but not of that kind. She took a long sip of her tea.

“Mx. Clay?”

Jester nodded slowly.

“Ah. I can see why. Is it true what they say about firbolgs?” 

Giggling, Jester said, “It is.”  
\----------  
After tea and pleasantries with the guests, Jester sat at her easel in the little library they had, a small sunlit room lined with bookshelves and over-stuffed chairs. In the center of the room was one large green couch Jester had fucked at least three guards on, and one man who worshipped Ioun and was into the idea of fucking in a library.

She began working on the picture of Mollymauk, sketching it out and starting to mix the paints. She was layering on the first bit of his skin when someone knocked on the door. “Come in,” Jester said.

Cali poked her head inside. “Oh. You busy?”

“Not too busy. Just don’t disturb my painting and you’ll be fine.”

“Alright.” Cali and Caduceus slipped inside, sitting on the couch. “What you painting?”

“Another client,” said Jester. “I can’t let you look ‘cause you’ll recognize them.”

“Oh, okay,” Cali said, nodding. She sat down on the couch, and Caduceus sat down next to her. They rubbed her thigh with a big paw, pushing up the hem of her dress to reveal a scaled thigh and black boots. Cali pressed their hand down. “Not now.”

“Don’t worry about me,” said Jester. “I’ll be busy painting. You two enjoy yourself.” She said this in part a little jealous, in part really curious to see them fuck. 

“See?” said Caduceus. “She doesn’t mind.” They put their hand back and kissed her.

“Fine, fine,” said Cali. “Only because she said so.” Cali kissed him back and pulled him close.

Jester smiled watching them. They were both so pretty...Her heart panged. She really liked both of them. Gods, what was she doing? She went back to painting, but she kept an ear out.

The two kissed and held each other, slowly getting more and more heated up. Their hand went up her skirt and down her underwear, rubbing at her clit. Jester paused in her painting, watching, transfixed, as Cali moaned softly. The two girls locked eyes and Cali said, “You like what you see, baby girl?”

Her voice was...wow. It came out of nowhere, but it set Jester’s cunt alight. “Yes, I do, Miss Cali.”

“Good,” said Cali with a smile. To Caduceus, she said, “My dear, be a good one and take off my panties, will you?”

Caduceus nodded and obeyed, taking off the panties and tossing them aside.

“Lock the door,” Cali added. “Can the door be locked?” she asked Jester.

“Yes, Miss Jester.” Jester nodded.

“Good girl,” said Cali. Caduceus stood and locked the library door while Cali leaned against the corner of the couch, legs spread, showing off her scales, which were slightly shifted open, and that pretty clit. She rubbed her clit idly while watching Caduceus return to her. “Why don’t you strip, my dear?”

“Yes, Miss Cali,” said Caduceus. They undid their pretty green robes, revealing their corset. “Shall I keep the corset on or no?”

“Keep it on. You look lovely.” Cali cast a glance at Jester. “I think she likes it.”

Jester blushed, going back to her painting.

“Don’t pretend you don’t, baby girl,” said Cali. She turned back to Caduceus. “Why don’t you come here and suck my clit until I’m ready for you?”

“Yes, Miss Cali,” said Caduceus, bending down on their knees and diving in. 

Cali moaned. “Fuck, dearest. You’ve got a talented tongue.”

Meanwhile, Jester was dying. She wanted to rub her cunt so bad. “Miss Cali,” she asked, “can I touch myself?”

“Finish that painting and you can,” said Cali. “Don’t rush, though. I expect perfection from you, Jester.”

“Yes, Miss Cali.” Jester obeyed, painting carefully with a steady hand. 

“Good girl.” Cali took in a sharp breath, shaking slightly. “Gods. Dearest, keep going, like that...gods.” She looked down. “I should be opened up all the way. Gods, I want that cock in me.”

“Yes, Miss Cali,” said Caduceus. They were already half-hard, growing harder with every touch from Cali. 

“You wanna come right now, don’t you?” asked Cali, as she lightly licked the top of his cock. “Like you did our first time, all over my face before going in me, right?”

Caduceus nodded. “Yes, ma’am. Please, ma’am.”

“Not yet, dearest,” Cali said, before leaning back and spreading her legs. “You’re coming in me, my sweet.”

Obediently, Caduceus knelt down, then slowly slipped into Cali’s cunt. Cali moaned, bucking up against Caduceus as they began to slowly fuck her.

Gods, Jester had never been so tempted to touch herself in her life. The two lovers made such wonderful moans, and they looked absolutely gorgeous together, intertwined like that. But she was a good girl, and she was determined to finish the painting.

Cali’s orgasm came slowly, slowly, then Caduceus reached down and rubbed her clit and it came all at once. Jester could practically smell her slick. She panted and said, “That was good. Good dear. Now, why don’t you come inside of me, sweetheart?”

Immediately, Caduceus began to properly plow into Cali, making her moan and cry out, while they grunted and groaned. Every sound the two made was glorious to Jester’s ears. Their bodies slammed into each other as they fucked, making a delightful noise. But Jester was good and worked on her painting.

With a grunt and a cry, Caduceus and Cali came at the same time. Caduceus pulled out, and Jester watched as her scales closed up all perfectly. “Good dear,” said Cali sweetly. She pulled Caduceus down for a kiss, then turned towards Jester. “Did you enjoy that?”

“Yes, Miss Cali!” said Jester. 

“Good girl.”  
\----------  
That night, Caleb came up a little early to the room. He stayed dressed, at least for now, sitting down in the over-stuffed chair by her bed. Jester sat in her drawing chair, practicing drawing the furniture in her room. Her right arm was cramping after so much drawing and painting, but it was a good kind of pain. A satisfying kind of pain. She liked it, though she had to stop every five minutes to massage the tension from her arm. 

A few minutes later, Molly arrived. They saw Jester, not sitting in her usual spot, then saw Caleb, sitting where they were supposed to sit, and asked, “What in the nine hells is going on?”

“We need to talk,” said Caleb, standing to offer his seat. “Mind if I sit on the bed?” he asked Jester.

“Feel free,” said Jester, pausing in her drawing for a moment so she could properly supervise the conversation.

“Okay…” Molly sat down, as did Caleb. “What is this about?”

“After what happened with that lady...you just shut me out.” Caleb’s face was soft, worried. “I’ve been concerned about you. Worried. We have a lot riding on this marriage. I want to make it work.”

“Ugh, are you gonna rattle my ear off again about the peace treaties and the trade deals and all those other arrangments?” Molly scoffed. “Is that all you want me for? What I can provide for you?” They sneered. “What they say about House Widogast is true. You really are heartless bastards.” 

They stood to leave, and Jester almost stood to interrupt them, but Caleb reached out a hand to steady them. “Nein. It’s not just about trade deals. I...I like you. I really do. You are...an amazing, beautiful person. It’s just that...I’m not sure I deserve you.”

Molly stopped, looking down at Caleb in shock. “You...really feel that way.”

“Ja. I do.” Caleb shook his head. “I don’t deserve you. I’m not very attractive, I’ve done...bad things. I’m not as good with words as you are. I’m just...I’m nothing, compared to you.”

Sadly, Molly laughed. “I mean...I thought I didn’t deserve you.”

Caleb looked up at them in shock. “How? You’re so amazing and wonderful...I’m nothing compared to you.”

“I’m broken, Caleb,” said Molly, frankly. “Before two years ago, I have no memory of what happened. I have a past I don’t even recognize, a past that could be really bad for all I know.” They wiped away tears from their eyes. “I came into my position by sheer luck. I don’t deserve it. I don’t deserve you.”

After a moment of shock, Caleb laughed. “Listen to how ridiculous we are. We’re arguing about thinking that neither of us deserves each other.”

Slowly, Molly laughed too. “It is pretty ridiculous.”

“It is,” said Caleb. The two calmed and settled into the moment. “Why don’t we try again. Forget all this not deserving each other stuff and have a proper go at it. What do you say?”

Molly nodded. “I think I’d like that.”

The two stared at each other silently. When Jester couldn’t bear it, she whispered dramatically, “Now this is where you kiss each other.”

Caleb and Molly giggled a little, a bit nervous. Then Molly slowly leaned in and kissed Caleb, kissed him softly, holding both cheeks like it was something precious. They pulled away for a moment. “That good?” Molly asked.

“Ja. Really good.” Caleb grinned and pushed in, kissing Mollymauk this time. Their kisses slowly got heated, and then hands began probing and wandering, then they started pulling at clothing and--

“I’m gonna go to the library so you can have your privacy,” said Jester.

“Oh,” said Caleb. “Ja. Danke.”

“Not a problem. Have fun! Tell me all about it tomorrow.” She waved at the two and went downstairs to work on more paintings.


	7. two shades of dark hair

**Notes for the Chapter:**

> Short chapter today!

Jester’s session of painting was interrupted by a knock at the library door. “Come in,” she said, almost singing the words, in a pretty good mood despite her tiredness.

Beau’s head popped in. “Okay, it’s just you,” she said, slipping in and closing the door. “I need a favor from you.”

“Okay…” Jester set down her paintbrush and watched as Beau sat down on the couch.

“I need another appointment with you again, but I don’t want to like...be with you.”

“Why?” Jester cocked her head in confusion.

“Because I want to be with Yasha, but my parents are here and we’re sharing a room so I have no privacy, and everywhere else is...too risky.”

“Oh. Okay, sure. Consider it done.”

“Thank you so much,” said Beau. She sighed and relaxed a little. “It’s been so long since we’ve fucked and...gods, I really think I’m in love with her.”

“Yeah?” Jester went back to painting. She was working on Caleb’s now, having finished Beau’s painting last night. 

“Yeah. Like...if I could marry her I would.”

“Wow.” 

“I know.” Beau shook her head. “But my parents would hate me for it. They’d disown me if I didn’t follow their well-laid plans.”

Jester shook her head. “I think you should follow your heart,” said Jester. “You’d have House Lavorre on your side, trust me. And if Yasha is really Molly’s favorite, you’d probably have House Tealeaf and House Widogast behind you, too.”

Beau nodded. “Maybe. I dunno. I might talk to Astrid about it. I’d hate to leave her with my mess. She’s not the woman for me, but she’s a decent human being, at least, and she doesn’t deserve to be abandoned just because I’m in love with someone else.”

“That’s fair.” Jester nodded.

“So...tonight? I’ll come in first and then invite Yasha up. Sound good?”

“Sure. I’ll bring my easel so I can paint while you’re at it.”

“Thank you so much. I owe you a big one.”

“Don’t even think about it,” said Jester. “We’re friends. Friends don’t let friends go without boning the ones they’re in love with.”

With a snicker, Beau got up and left the room.  
\----------  
Beau came in that night, and Yasha came right after her. As soon as the two were in a room together, and Jester was occupied with her painting, the two were all over each other, kissing and grabbing and whispering how much they loved each other.

Jester didn’t watch or listen in as she did with Cali and Caduceus. She hadn’t really been included, so she wasn’t going to peep in on them. She just focused on her painting. 

But at least they seemed to be having fun, she figured.


End file.
